EP1339730A2 - Macrolide solvates - Google Patents
Macrolide solvatesInfo
- Publication number
- EP1339730A2 EP1339730A2 EP01997498A EP01997498A EP1339730A2 EP 1339730 A2 EP1339730 A2 EP 1339730A2 EP 01997498 A EP01997498 A EP 01997498A EP 01997498 A EP01997498 A EP 01997498A EP 1339730 A2 EP1339730 A2 EP 1339730A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- azithromycin
- water
- monohydrate
- weeks
- sample
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Definitions
- the present invention relates to macrolide solvates, i.e. solvates of azithromycin and similar compounds.
- Azithromycin (9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin A) is a well- known antibacterial agent, described e.g. in The Merck Index, 12 th edition (1996), page 157 (item 946) and may be produced according to a known process.
- Azithromycin may be obtained in the form of a solvate, e.g. in the form of a hydrate, such as a monohydrate or e.g. in the form of a dihydrate.
- azithromycin in the form of a monohydrate may be unstable and may contain degradation products, when set out to normal air humidity conditions and azithromycin in the form of a monohydrate produced according to known methods, e.g. by precipitation with water from an ethanolic solution, may beside its instability contain a high content of residual solvents.
- azithromycin currently on the market is in the form of a dihydrate which is known to be stable under normal air humidity conditions.
- azithromycin may be obtained in the form of a, e.g. crystalline, monohydrate which is stable.
- the present invention provides azithromycin in the form of a monohydrate comprising from 4.0% to 6.5% w/w of water.
- Azithromycin in the form of a monohydrate comprising from 4.0% to 6.5% w/w of water is hereinafter designated as "azithromycin according to the present invention.
- Azithromycin according to the present invention contains water from 4.0% to 6.5%.
- the calculated amount of water in azithromycin in the form of a composition consisting of 1 mol of azithromycin and 1 mol of water is around 2.35% w/w, but an azithromycin/water composition wherein the water content is different from 2.35% w/w, does not necessarily mean that the crystallisation form of azithromycin is different from the crystallisation form of azithromycin in the form of a monohydrate.
- the X-ray powder diffraction pattern of azithromycin according to the present invention is corresponding to the X-ray powder diffraction pattern which is disclosed for azithromycin in the form of a monohydrate as disclosed in EP 941 999, Figure 2, and EP 984020, Figure 2; and is substantially different from the X-ray powder diffraction pattern of azithromycin in the form of a dihydrate as disclosed in EP 941 999, Figure 1, and in EP 984020, Figure 4.
- Azithromycin according to the present invention is substantially crystalline and maintains its X-ray powder diffraction pattern, i.e. it maintains its crystalline structure, within at least 2 weeks, e.g. up to 6 weeks and more, such as 2 to 6 weeks, under normal, e.g. normal air, humidity conditions, e.g. even at elevated temperatures.
- Azithromycin according to the present invention may be further defined by its low content of azithromycin degradation products.
- normal e.g. normal air
- humidity conditions such as 70% to 80%, e.g. 75% humidity
- within 2 to 6 weeks e.g. within 6 weeks
- temperatures e.g. 35°C to 45°C, such as 40°C; e.g.
- azithromycin according to the present invention under a temperature of 40°C in an environment of 75% humidity within 6 weeks is less than 2.0%, even less than 1.0% and even less than 0.5%, namely (around) 0.1%, whereas azithromycin in the form of a monohydrate having a water content of 2.8% to 3.6% shows a degradation of 2.5% already within 2 weeks, which degradation is increasing within 4 weeks, and is of almost 7% within 6 weeks under the same conditions.
- the present invention provides azithromycin in the form of a monohydrate, characterized in that in a sample thereof the degradation of azithromycin is less than 2%, even less than 1.5%, such as 0.05% to 1.0%, e.g. 0.05 to 0.5%, when setting out said sample to normal, e.g. normal air, humidity conditions, such as 75% envionmental humidity, e.g. at elevated temperatures, such as of 40°C, within at least 2 weeks, e.g within 2, e.g. 4, and e.g. even 6 weeks.
- normal e.g. normal air
- humidity conditions such as 75% envionmental humidity, e.g. at elevated temperatures, such as of 40°C
- Azithromycin degradation which occurs under the above described conditions in a sample of azithromycin according to the present invention is within the percentage range of degradation products allowed by Pharmacopeiias in commercial azithromycin forms.
- Azithromycin according to the present invention may be further defined by its stable water content.
- the water content practically does not increase, e.g. the water content remains essentially the same, when setting out said sample to normal, e.g. normal air, humidity conditions, such as 70% to 80%, e.g. 75% humidity, within 6 weeks, e.g. within 4 to 6 weeks, and even longer, e.g. at elevated temperatures, such as temperatures above room temperatures, e.g. 35°C to 45°C, such as 40°C; e.g. we have found that the water content of azithromycin according to the present invention at a temperature of 40°C, in an environment of 75% humidity remains substantially the same as in week 0 within 4 weeks and even 6 weeks.
- the present invention provides azithromycin in the form of a monohydrate, characterized in that in a sample thereof the water content remains substantially the same as in week 0, when setting out said sample to normal, e.g. normal air, humidity conditions, such as 75% envionmental humidity, e.g. at elevated temperatures, such as temperatures above room temperatures, e.g. 35°C to 45°C, e.g. 40°C, for a period of 4 weeks, e.g. 4 to 6 weeks.
- normal e.g. normal air
- humidity conditions such as 75% envionmental humidity
- Azithromycin according to the present invention may be obtained e.g. as follows: Azithromycin in any form, e.g. in free base form; and in the form of a salt, e.g. in the form of a hydrochloride, e.g. a dihydrochloride, acetate; and/or in the form of a solvate, e.g.in the form of a monohydrate, having a water content which is different from 4.0% to 6.5%, in anhydrous form, or in the form of a dihydrate, preferably in the form of a salt, may be e.g. used as a starting material.
- a solution of azithromycin in the form of a salt in a solvent may be produced, e.g.
- a “solution” includes a suspension, in which at least a part of azithromycin (e.g. in the form of a salt) is dissolved.
- Appropriate acids include organic acids, for example formic acid or acetic acid, and inorganic acids, for example hydrochloric, hydrobromic, nitric or sulphuric acid, preferably hydrochloric acid or sulphuric acid.
- Solvent includes solvent which is appropriate to dissolve azithromycin in the form of a salt, e.g.
- Aqueous solvent includes water or a mixture of water with organic solvent, e.g. one or more organic solvents, for example water miscible and water immiscible organic solvent, such as alcohols, e.g. methanol, ethanol, isopropanol; ketones such as acetone, methyl isobutyl ketone; alkyl carboxylic acid esters, e.g. (C ⁇ - 4 )alkyl carboxylic acid esters, of formic or acetic acid, e.g.
- water, or aqueous solvent such as water or water containing 0.5% to 20 % v/v; such as 1 % to 15 % v/v of organic solvent. It is one advantage of the present invention that water in the absence of organic solvent may be used.
- Appropriate reaction conditions for the production of a solution of azithromycin in the form of a salt according to the process of the present invention include, e.g. (i) A temperature at which azithromycin is not degraded, e.g. including a temperature range of -20°C to 90°C , such as 0°C to 70°C, (ii) An appropriate pressure, e.g. atmospheric pressure, and a pressure which is above or below atmospheric pressure; (iii) Appropriate dilution, e.g. a dilution range of 1 g to 500 g of azithromycin in the form used as a starting material, per litre of solvent.
- a resulting solution of azithromycin in the form of a salt in a solvent may be optionally purified as appropriate, e.g. by filtration, charcoal treatment; in order to remove impurities.
- the pH of an, e.g. purified, solution of azithromycin in the form of a salt may be adjusted to an pH where azithromycin is present in free form, including e.g. a pH of, e.g. ca., 8.0 to 13.0, such as 9.0 to 12.0, e.g. 10.0 to 11.0; e.g. by addition of a base to a solution of azithromycin in the form of a salt in a solvent.
- a “solution" of azithromycin in free form includes a suspension, in which at least a part of azithromycin is dissolved.
- Appropriate bases include bases which are suitable for pH adjustment, e.g. inorganic bases, such as ammonia or alkali-, e.g. sodium, potassium; earth alkali-, e.g. calcium-, magnesium-; and ammonium-
- a base is preferably a hydroxide, e.g. sodium, or ammonia; preferably in aqueous solution.
- Azithromycin in free form and in the form of a stable crystalline monohydrate may precipitate from the solution and may be isolated, e.g. analogously to a method as conventional, e.g. by centrifugation or filtration; and may be dried at appropriate temperatures, e.g. including a temperature range of 20°C to 80°C, e.g. under atmospheric pressure or under vacuum; until a water content of 4.0% to 6.5% is achieved. Crystalline azithromycin in the form of a monohydrate may be obtained comprising from 4.0% to 6.5% of water.
- the present invention provides a process for the production of azithromycin in the form of a monohydrate comprising from 4.0% to 6.5% of water, said process comprising the steps
- substantially free of organic solvent When solely water is used as a solvent azithromycin according to the present invention may be obtained, substantially free of organic solvent.
- substantially free includes an analytically undetectable amount up to an analytically detectable amount of 0.5% w/w of organic solvent; which is an amount of organic solvents; which is within the range which European Pharmacopoeiias define as appropriate for pharmaceutical ingredients, e.g for solvents whith low toxic potential (Class 3 solvents).
- the present invention provides azithromycin in the form of a crystalline monohydrate, which is substantially free of organic solvent.
- Azithromycin according to the present invention is useful in the production of a pharmaceutical composition comprising azithromycin as an active ingredient.
- the present invention provides a pharmaceutical composition, comprising, e.g. essentially consisting of, azithromycin according to the present invention in association with at least one pharmaceutical carrier or diluent.
- a pharmaceutical composition according to the present invention may contain the same concentrations of azithromycin and may be used for the same indications in the same dosage ranges as a known pharmaceutical composition comprising azithromycin in the form of a dihydrate, e.g. as is currently on the market. Examples
- the X-ray powder diffraction pattern of azithromycin in the form of a monohydrate obtained according to the following example corresponds to that of azithromycin in the form of a monohydrate.
- Azithromycin in the form of a monohydrate obtained according to the following example maintains its crystallinity and its X-ray powder diffraction pattern and contains substantially no degration products when kept for 6 weeks under normal air humidity conditions at elevated temperatures.
- the X-ray diffraction powder pattern of azithromycin obtained corresponds to the X-ray diffraction powder pattern of azithromycin in the form of a monohydrate as disclosed in EP 941 999, Figure 2, and EP 984 020, Figure 2 on day 1 , on day 2 and on day 13.
- Crystalline azithromycin in both samples shows a X-ray powder diffraction pattern corresponding to that of azithromycin in the form of a monohydrate according to EP 941
Abstract
Description
Claims
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US25311900P | 2000-11-27 | 2000-11-27 | |
US253119P | 2000-11-27 | ||
GB0031355A GB0031355D0 (en) | 2000-12-21 | 2000-12-21 | Organic compounds |
GB0031355 | 2000-12-21 | ||
PCT/EP2001/013760 WO2002042315A2 (en) | 2000-11-27 | 2001-11-26 | Macrolide solvates |
Publications (1)
Publication Number | Publication Date |
---|---|
EP1339730A2 true EP1339730A2 (en) | 2003-09-03 |
Family
ID=26245472
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
EP01997498A Withdrawn EP1339730A2 (en) | 2000-11-27 | 2001-11-26 | Macrolide solvates |
Country Status (15)
Country | Link |
---|---|
US (1) | US6949519B2 (en) |
EP (1) | EP1339730A2 (en) |
JP (1) | JP2004519430A (en) |
KR (1) | KR100815163B1 (en) |
AU (1) | AU2002221895A1 (en) |
BG (1) | BG66200B1 (en) |
CA (1) | CA2429639C (en) |
CZ (1) | CZ303343B6 (en) |
EE (1) | EE05200B1 (en) |
HR (1) | HRP20030430B1 (en) |
HU (1) | HU229488B1 (en) |
NO (1) | NO324951B1 (en) |
PL (1) | PL207076B1 (en) |
SK (1) | SK287814B6 (en) |
WO (1) | WO2002042315A2 (en) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HRP20020231A2 (en) * | 2002-03-18 | 2003-12-31 | Pliva D D | ISOSTRUCTURAL PSEUDOPOLYMORPHS OF 9-DEOXO-9a-AZA-9a-METHYL-9a-HOMOERYTHROMYCIN A |
AU2002256846B2 (en) | 2001-05-22 | 2007-04-05 | Pfizer Products Inc. | Crystal Forms of Azithromycin |
US6861413B2 (en) | 2001-05-22 | 2005-03-01 | Pfizer Inc. | Stable non-dihydrate azithromycin oral suspensions |
GB0214277D0 (en) * | 2002-06-20 | 2002-07-31 | Biochemie Gmbh | Organic compounds |
US6855813B2 (en) | 2002-07-19 | 2005-02-15 | Alembic Limited | Process for the preparation of azithromycin monohydrate |
HRP20020614A2 (en) | 2002-07-22 | 2004-06-30 | PLIVA-ISTRAŽIVAČKI INSTITUT d.o.o. | Rhombic pseudopolymorph of 9-deoxo-9a-aza-9a-methyl-9a-homoerythromycin a |
GB0224197D0 (en) * | 2002-10-17 | 2002-11-27 | Biochemie Gmbh | Organic compounds |
EP1606299A1 (en) * | 2003-03-25 | 2005-12-21 | Teva Pharmaceutical Industries Ltd. | Degradation products of azithromycin, and methods for their identification |
US20050101547A1 (en) * | 2003-11-06 | 2005-05-12 | Sadatrezaei Mohsen | Stabilized azithromycin composition |
US7943585B2 (en) | 2003-12-22 | 2011-05-17 | Sandoz, Inc. | Extended release antibiotic composition |
US7384921B2 (en) | 2004-02-20 | 2008-06-10 | Enanta Pharmaceuticals, Inc. | Polymorphic forms of 6-11 bicyclic ketolide derivatives |
US20060116336A1 (en) * | 2004-03-17 | 2006-06-01 | American Pharmaceutical Partners, Inc. | Lyophilized azithromycin formulation |
US7468428B2 (en) * | 2004-03-17 | 2008-12-23 | App Pharmaceuticals, Llc | Lyophilized azithromycin formulation |
US7683162B2 (en) * | 2004-08-30 | 2010-03-23 | Taro Pharmaceutical Industries Limited | Process of preparing a crystalline azithromycin monohydrate |
JP4471941B2 (en) * | 2005-03-10 | 2010-06-02 | 山一電機株式会社 | Socket for semiconductor device |
US20090318375A1 (en) * | 2005-06-08 | 2009-12-24 | Hanmi Pharm Co., Ltd | Crystalline Azithromycin L-Malate Monohydrate and Pharmaceutical Composition Containing Same |
EP2405909A1 (en) | 2009-03-13 | 2012-01-18 | Da Volterra | Compositions and methods for elimination of gram-negative bacteria |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4474768A (en) | 1982-07-19 | 1984-10-02 | Pfizer Inc. | N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor |
US4517359A (en) | 1981-03-06 | 1985-05-14 | Sour Pliva Farmaceutska, Kemijska Prehrambena I Kozmeticka Industrija, N.Sol.O. | 11-Methyl-11-aza-4-0-cladinosyl-6-0-desosaminyl-15-ethyl-7,13,14-trihydroxy-3,5,7,9,12,14-hexamethyl-oxacyclopentadecane-2-one and derivatives thereof |
EP0298650A2 (en) * | 1987-07-09 | 1989-01-11 | Pfizer Inc. | Azithromycin dihydrate |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1989002271A1 (en) * | 1987-09-10 | 1989-03-23 | Pfizer | Azithromycin and derivatives as antiprotozoal agents |
PT102006B (en) * | 1997-05-19 | 2000-06-30 | Hovione Sociedade Quimica S A | NEW AZITROMYCIN PREPARATION PROCESS |
PT102130A (en) * | 1998-03-13 | 1999-09-30 | Hovione Sociedade Quimica S A | METHOD FOR PREPARING AZITHROMYCY DIHYDRATE |
CA2245398C (en) | 1998-08-21 | 2002-01-29 | Apotex Inc. | Azithromycin monohydrate isopropanol clathrate and methods for the manufacture thereof |
HUP0104241A3 (en) * | 1998-11-30 | 2003-12-29 | Teva Pharma | Ethanolate of azithromycin, process for manufacture, and pharmaceutical compositions |
EP1712556B1 (en) * | 1999-06-29 | 2010-06-02 | Sandoz AG | Azithromycin monohydrate |
ES2177373B1 (en) * | 1999-11-26 | 2003-11-01 | Astur Pharma Sa | PREPARATION OF AZITHROMYCIN IN ITS NON-CRYSTALLINE FORM |
-
2001
- 2001-11-26 HU HU0302099A patent/HU229488B1/en not_active IP Right Cessation
- 2001-11-26 CZ CZ20031439A patent/CZ303343B6/en not_active IP Right Cessation
- 2001-11-26 PL PL361276A patent/PL207076B1/en unknown
- 2001-11-26 US US10/432,545 patent/US6949519B2/en not_active Expired - Fee Related
- 2001-11-26 SK SK635-2003A patent/SK287814B6/en not_active IP Right Cessation
- 2001-11-26 EE EEP200300255A patent/EE05200B1/en not_active IP Right Cessation
- 2001-11-26 KR KR1020037006623A patent/KR100815163B1/en not_active IP Right Cessation
- 2001-11-26 JP JP2002544448A patent/JP2004519430A/en not_active Withdrawn
- 2001-11-26 WO PCT/EP2001/013760 patent/WO2002042315A2/en active Application Filing
- 2001-11-26 EP EP01997498A patent/EP1339730A2/en not_active Withdrawn
- 2001-11-26 AU AU2002221895A patent/AU2002221895A1/en not_active Abandoned
- 2001-11-26 CA CA002429639A patent/CA2429639C/en not_active Expired - Fee Related
-
2003
- 2003-05-21 BG BG107832A patent/BG66200B1/en unknown
- 2003-05-26 HR HR20030430A patent/HRP20030430B1/en not_active IP Right Cessation
- 2003-05-26 NO NO20032371A patent/NO324951B1/en not_active IP Right Cessation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4517359A (en) | 1981-03-06 | 1985-05-14 | Sour Pliva Farmaceutska, Kemijska Prehrambena I Kozmeticka Industrija, N.Sol.O. | 11-Methyl-11-aza-4-0-cladinosyl-6-0-desosaminyl-15-ethyl-7,13,14-trihydroxy-3,5,7,9,12,14-hexamethyl-oxacyclopentadecane-2-one and derivatives thereof |
US4474768A (en) | 1982-07-19 | 1984-10-02 | Pfizer Inc. | N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor |
EP0298650A2 (en) * | 1987-07-09 | 1989-01-11 | Pfizer Inc. | Azithromycin dihydrate |
Non-Patent Citations (1)
Title |
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See also references of WO0242315A2 |
Also Published As
Publication number | Publication date |
---|---|
AU2002221895A1 (en) | 2002-06-03 |
KR20030055305A (en) | 2003-07-02 |
US6949519B2 (en) | 2005-09-27 |
WO2002042315A2 (en) | 2002-05-30 |
EE05200B1 (en) | 2009-08-17 |
HRP20030430B1 (en) | 2011-11-30 |
KR100815163B1 (en) | 2008-03-19 |
CA2429639C (en) | 2009-07-14 |
HRP20030430A2 (en) | 2005-04-30 |
US20040053862A1 (en) | 2004-03-18 |
NO324951B1 (en) | 2008-01-14 |
NO20032371D0 (en) | 2003-05-26 |
BG107832A (en) | 2004-07-30 |
EE200300255A (en) | 2003-08-15 |
HU229488B1 (en) | 2014-01-28 |
WO2002042315A3 (en) | 2002-10-31 |
BG66200B1 (en) | 2012-01-31 |
CZ20031439A3 (en) | 2003-10-15 |
HUP0302099A3 (en) | 2009-08-28 |
CA2429639A1 (en) | 2002-05-30 |
PL361276A1 (en) | 2004-10-04 |
JP2004519430A (en) | 2004-07-02 |
SK287814B6 (en) | 2011-11-04 |
PL207076B1 (en) | 2010-10-29 |
CZ303343B6 (en) | 2012-08-08 |
HUP0302099A2 (en) | 2003-10-28 |
NO20032371L (en) | 2003-07-10 |
SK6352003A3 (en) | 2003-11-04 |
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